Technology Process of (2S,10R,14S,3Z,11Z)-15-methyl-2,10,14-tribenzyloxyhexadeca-3,11-dien-6-one
There total 16 articles about (2S,10R,14S,3Z,11Z)-15-methyl-2,10,14-tribenzyloxyhexadeca-3,11-dien-6-one which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
(2S,6S,10R,14S,3Z,11Z)-15-methyl-2,10,14-tribenzyloxyhexadeca-3,11-dien-6-ol;
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
at -60 ℃;
for 0.25h;
Inert atmosphere;
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at -60 ℃;
for 0.0833333h;
Inert atmosphere;
DOI:10.1016/j.tet.2010.10.045
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 80 percent / trifluoroacetic acid
2: 71 percent / diisobutylaluminum hydride / 0 °C
3: 1.) DMSO, (COCl)2, 2.) Et3N / CH2Cl2
4: 97 percent
5: diisobutylaluminum hydride / -78 °C
6: 1.) NaH
7: 98 percent / toluene / Heating
9: 86 percent / NaH, Bu4NI / tetrahydrofuran
10: 1.) 9-borabicyclo<3.3.1>nonane, 2.) H2O2, NaOH / 1.) THF
11: 1.) DMSO, (COCl)2, 2.) Et3N
12: 76 percent / SnCl4
13: 1.) DMSO, (COCl)2, 2.) n-Pr2NEt
With
sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dipropylethylamine; dihydrogen peroxide; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; toluene;
DOI:10.1016/0040-4039(93)85037-W
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 80 percent / trifluoroacetic acid
2: 71 percent / diisobutylaluminum hydride / 0 °C
3: 1.) DMSO, (COCl)2, 2.) Et3N / CH2Cl2
4: 97 percent
5: diisobutylaluminum hydride / -78 °C
6: 1.) NaH
7: 98 percent / toluene / Heating
9: 86 percent / NaH, Bu4NI / tetrahydrofuran
10: 1.) 9-borabicyclo<3.3.1>nonane, 2.) H2O2, NaOH / 1.) THF
11: 1.) DMSO, (COCl)2, 2.) Et3N
12: 76 percent / SnCl4
13: 1.) DMSO, (COCl)2, 2.) n-Pr2NEt
With
sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dipropylethylamine; dihydrogen peroxide; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; toluene;
DOI:10.1016/0040-4039(93)85037-W
